Simple and Clean Procedure for Three‐Component Syntheses of Spiro{pyrido[2,1‐<i>b</i>]benzothiazole‐3,3′‐indolines} and Spiro{thiazolo[3,2‐<i>a</i>]pyridine‐7,3′‐indolines} in Aqueous Medium

Hussein, Essam M.; El‐Khawaga, Ahmed M.

doi:10.1002/jhet.908

Cited by 15 publications

(6 citation statements)

References 13 publications

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“…Based on these prior observations, we postulated that a Schiff base containing both indoline and pyran pharmacophores could be very effective for antimicrobial and anticancer activity. In this paper and as a consequence of our previous work on the green synthesis of different spiroheterocyclic (Hussein 2013 ; Hussein and El-Khawaga 2012 ; Hussein 2012 ; El-Zohry et al 2008b , c , 2009 ), and bioactive heterocyclic compounds (Hussein et al 2015b ; Hussein and Abdel-Monem 2011 ), we investigated a novel green and efficient protocol that was developed for the synthesis of some Schiff bases ( 5a – l ) by the condensation of spiro[indoline-3,4′-pyran]-3′-carbonitrile derivatives ( 3a – c ) with aromatic aldehydes ( 4a – d ) using ammonium chloride (10 mol%) in refluxing ethanol as shown in Scheme 2 and Table 1 . The antimicrobial and cytotoxic properties of the prepared compounds were screened.…”

Section: Introductionmentioning

confidence: 72%

Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

et al. 2016

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BackgroundIndolinone and spiro-indoline derivatives have been employed in the preparation of different important therapeutic compounds required for treatment of anticonvulsants, antibacterial, Antitubercular, and anticancer activities. Schiff bases have been found to possess various pharmacological activities such as antitubercular, plant growth inhibiting, insecticsidal, central nerve system depressant, antibacterial, anticancer, anti-inflammatory, and antimicrobial. Mannich bases have a variety of biological activities such as antibacterial and antifungal activities.ResultsIn this study, a green, rapid and efficient protocol for the synthesis of a new series of Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitrile derivatives using ammonium chloride as a very inexpensive and readily available reagent. The prepared compounds were assessed in vitro for their antimicrobial activity. Also, the cytotoxic activity of the prepared compounds was assessed in vitro against human cells line MCF7 breast cancer.ConclusionGood activity was distinguished for Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles, with some members recorded higher antimicrobial and anti-breast cancer activities.Graphical abstractNovel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles

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Section: Introductionmentioning

confidence: 72%

Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

et al. 2016

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“…A simple and efficient one‐pot three components synthesis of spiro[thiazolo[3,2‐ a ]pyridin]‐7,3'‐indoline derivatives was carried out from the reaction of 2‐mercaptoacetic acid, malononitrile, and a series of 2‐oxoindoline‐3‐ylidines in aqueous medium. This method is of great value because of its environmentally benign character, high yielding process, and easy handling (Scheme ).…”

Section: Condensed 4‐thiazolidinonesmentioning

confidence: 99%

Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Gupta

2015

Journal of Heterocyclic Chem

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The syntheses of condensed 4‐thiazolidinone and its various derivatives are reviewed for the first time. Condensed 4‐thiazolidinones are important scaffolds and versatile substrates in heterocyclic chemistry, as they can be used for the synthesis of a large variety of biologically active compounds such as thiazolotriazines and as raw material for the drug synthesis. The high reactivity of active methylene group next to the carbonyl of the thiazolidin ring represents useful targets for many organic reactions.

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“…The view of our design of the newly synthesized compounds in this research point is based on other biologically active heterocycles reported in the field of microbial and cancer therapy such as pyrazoles [15,16], triazoles [17,18], and Schiff bases [19][20][21]. In continuation of our work on the synthesis of heterocyclic systems [22][23][24][25] and for biological evaluations [26,27], we considered it attractive to synthesize some novel substituted 6′-(4-chlorophenyl)-3,4′-bipyridine-3′-carbonitriles and evaluation of their antimicrobial and cytotoxic activity. 2-(6′-(4-Chlorophenyl)-3′-cyano-3,4′-bipyridin-2′-yloxy) acetohydrazide (3) was prepared and used as a building block for the synthesis of the title compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some novel 6′-(4-chlorophenyl)-3,4′-bipyridine-3′-carbonitriles: assessment of their antimicrobial and cytotoxic activity

Hussein¹,

Al-Shareef

Aboellil

et al. 2015

Zeitschrift Für Naturforschung B

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A series of novel substituted 6′-(4-chlorophenyl)-3,4′-bipyridine-3′-carbonitriles with incorporated pyrazole and/or triazole moieties have been synthesized using 2-(6′-(4-chlorophenyl)-3′-cyano-3,4′-bipyridin-2′-yloxy)acetohydrazide (3) as starting material. Also, the key intermediate 3 reacted with aromatic aldehydes and tosyl chloride to give the corresponding Schiff bases and tosyl hydrazide derivatives, respectively. The antimicrobial of these newly synthesized compounds was evaluated against Bacillus subtilis as Gram-positive bacteria and Trichoderma viride as a fungus; some of these compounds such as 5, 6, 7, 8, 10, 12, and 14 showed excellent activities as antimicrobial agents. Moreover, the cytotoxic activity of the most active compounds was assessed in vitro against human tumor liver cancer cell line (HEPG2); compounds 8, 10, 13a, and 14 showed potent activities relative to Doxorubicin which was used as a reference standard drug in this study.

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Simple and Clean Procedure for Three‐Component Syntheses of Spiro{pyrido[2,1‐b]benzothiazole‐3,3′‐indolines} and Spiro{thiazolo[3,2‐a]pyridine‐7,3′‐indolines} in Aqueous Medium

Cited by 15 publications

References 13 publications

Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Synthesis of some novel 6′-(4-chlorophenyl)-3,4′-bipyridine-3′-carbonitriles: assessment of their antimicrobial and cytotoxic activity

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